Elsevier

Tetrahedron

Volume 55, Issue 50, 10 December 1999, Pages 14243-14250
Tetrahedron

Hydroalumination of 3-butyn-1-ol: Application to a stereoselective synthesis of (3E,5Z)-3,5-dodecadienyl acetate, the sex pheromone of the leaf roller moth

https://doi.org/10.1016/S0040-4020(99)00899-6Get rights and content

Abstract

Hydroalumination-iodinolysis of 3-butyn-1-ol (2) provided E-4-iodo-3-buten-1-ol(4E) as the major product. This compound was transformed in three steps into the leaf roller moth sex pheromone 1 with high (>99% de) stereoselectivity and good overall yield (4 steps, 39% from 2).

Pheromone 1 may be prepared highly stereoselectively with hydroalumination of 3-butyn-1-ol as a key step.

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